The Boston Bruins could face a potentially complex dilemma over the Toronto Maple Leafs first-round pick in the 2026 NHL Draft.

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The Boston Bruins could face a potentially complex dilemma over the Toronto Maple Leafs first-round pick in the 2026 NHL Draft.

The Boston Bruins fleeced the Toronto Maple Leafs in the Brandon Carlo trade at last year’s deadline. That assertion has become a matter of public record.

In the deal, the Bruins landed Fraser Minten, a 2025 fourth-round pick, and the Maple Leafs’ first-round pick in the 2026 NHL Draft.

That’s where the potentially complex dilemma could lie.

It turns out that Toronto’s 2026 first-rounder is top-five protected. At the time of the trade, it didn’t seem like the Maple Leafs would tank this year. But it’s funny how things work out in the Bruins’ favor.

With the Maple Leafs’ playoff hopes hanging by a thread, Tankathon projects that first-round selection to be 14th overall. Under those circumstances, Boston gets the pick. End of story.

But if the Maple Leafs’ bottom out and enter the NHL Draft Lottery, that’s where things could get really dicey. As long as the Leafs get the sixth pick onwards, the Bruins receive the selection. Things could go haywire if Toronto gets picks one through five.

As a side note, the New York Islanders had the 10th overall pick in last year’s draft. The Islanders won the lottery and got the first-overall selection. So, it’s not beyond the realm of possibility that the Leafs get lucky in the lottery and move up to at least the fifth spot.

That’s where the Bruins will have to pay attention. The Bruins would then end up in a competition with the Philadelphia Flyers.

Bruins and Flyers Could Compete for Toronto’s 2027 1st-Rounder

Under the terms of the pick, if Toronto’s 2026 first-rounder falls in the top five, the Leafs get to choose whether they send their unprotected 2027 first-rounder to either the Bruins or Flyers.

All right, so the Bruins aren’t going to compete with the Flyers. They’ll just let Toronto figure out what to do.

That thought, well, might not be so cut and dry. The here is that, suppose the Maple Leafs continue to bottom out, and that pick lands in the top five again, the Flyers may be willing to throw something in to entice the Leafs to pick them.

That’s what insider Chris Johnston believes could be a possibility from what he’s heard. So, let’s say the Leafs finish in top-five territory next season, the Bruins could miss out on that pick and empty-netter up getting the Leafs 2028 first-round pick instead.

Would Boston Just Let Philadelphia Overpay?

There’s a possibility the Bruins could just sidestep the issue and allow the Flyers to overpay for the Leafs’ top pick. Incidentally, the Flyers landed a first-round pick from the Leafs in the Scott Laughton trade last season. The Leafs pledged their 2027 first-rounder, top-10 protected, in that trade.

That’s top 10 protection assumes the Bruins get the Leafs’ 2026 first-rounder. That’s the plan. Boston fans hope it stays that way. Tankathon projects the Bruins picking 22nd overall as a result of their own pick. That’s why adding a high first-rounder would make this year’s trade a potential home run.

But then again, things could get messy in a hurry. It’s an exercise worth keeping in mind as the remainder of the season plays out.

Nestor Quixtan Seasoned NHL analyst and baseball writer focused on covering clubs across each league with news, analysis, and insights. Originally from Toronto, Canada, Nestor’s singular experiences and background have enabled him to bring a different take on the sports world as a whole. Nestor’s fondness for baseball and hockey set the tone for his love and passion for writing about sports. More about Nestor Quixtan

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